149575-84-8Relevant articles and documents
CHLORSULFONATION OF N-PHENYLMORPHOLINE, BENZOTHIAZOLE, 2-METHYLBENZOTHIAZOLE AND TRIPHENYLOXAZOLE
Cremlyn, Richard J.,Bassin, Jatinder P.,Farouk, Sultan,Potterton, Michael,Mattu, Tajinder
, p. 107 - 120 (2007/10/02)
N-Phenylmorpholine (1) reacted with chlorosulfonic acid to give the p-sulfonyl chloride (2), which was characterized as the sulfonamides (3-5).Benzothiazole (6) was converted into the sulfonyl chloride (7) by sequential treatment with hot chlorosulfonic acid and thionyl chloride.Reaction of (7) with amines afforded the derivatives (8-10); NMR spectral analysis of the dimethylamide (8) indicated that it was a mixture of the 4- and 7-isomers.Chlorosulfonation of 2-methylbenzothiazole (11) was achieved by heating with chlorosulfonic acid with or without thionyl chloride.The chloride (12) was converted into amides (13-19).Study of the NMR spectra indicated that mixtures of the 5- and 6-isomers were formed. 2,4,5-Triphenyloxazole (20) reacted with chlorosulfonic acid to give either the mono-(21), bis (23) or bis-tris sulfonylchlorides (23, 34); these were converted into 14 sulfonamides. 2-(p-Nitrophenyl)-4,5-diphenyloxazole (41) reacted with hot chlorosulfonic acid to give the bis-sulfonyl chloride (42), characterized as the dimethylsulfonamide (43).Attempts to form the pure monosulfonyl chloride and to mono nitrate 2,4,5-triphenyloxazole (20) were unsuccessful.Key words: N-Phenylmorpholine; benzothiazole; 2-methylbenzothiazole; triphenyloxazole; chlorosulfonation